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Thiofanox | 75013-98-8

中文名称
——
中文别名
——
英文名称
Thiofanox
英文别名
[(E)-(3,3-dimethyl-1-methylsulfanylbutan-2-ylidene)amino] N-methylcarbamate
Thiofanox化学式
CAS
75013-98-8;39196-18-4
化学式
C9H18N2O2S
mdl
——
分子量
218.32
InChiKey
FZSVSABTBYGOQH-XFFZJAGNSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    14
  • 可旋转键数:
    5
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.78
  • 拓扑面积:
    76
  • 氢给体数:
    1
  • 氢受体数:
    4

ADMET

代谢
棉花植物的完全展开叶片在田间单独处理了(35)S标记的DIAMOND SHAMROCK (3,3-二甲基)-1-(甲基硫基)-2-丁酮O-(甲基碳氧基)肟)。形成了磺酰基和亚磺酰基。...由处理过的种子生长的幼苗得到了与成熟植物和土壤中获得的相同结果。
FULLY EXPANDED LEAVES OF COTTON PLANTS GROWN IN THE FIELD WERE TREATED INDIVIDUALLY WITH (35)S-LABELED DIAMOND SHAMROCK (3,3-DIMETHYL)-1-(METHYLTHIO)-2- BUTANONE O-(METHYLCARBOMYL) OXIME). THE SULFONE & SULFOXIDE WERE FORMED. ... SEEDLINGS GROWN FROM TREATED SEED GAVE SAME RESULTS AS THOSE OBTAINED IN MATURE PLANTS & IN SOIL.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在土壤中,DS-15647的化学变化与植物中发现的相似,但它们进行得更慢。在温室中种植的用DIAMOND SHAMROCK (3,3-二甲基)-1-(甲基硫基)-2-丁酮O-(甲基碳氧基)氧化物表面处理的棉花种子,在1天后吸收了20%的剂量。从用处理过的种子种植的植物中回收的主要产物是亚砜和砜衍生物。
IN SOIL THE CHEM CHANGES OF DS-15647 WERE SIMILAR TO THOSE FOUND IN PLANTS, BUT THEY PROCEEDED AT SLOWER RATES. COTTON SEEDS THAT HAD BEEN SURFACE TREATED WITH DIAMOND SHAMROCK (3,3-DIMETHYL)-1-(METHYLTHIO)-2-BUTANONE O-(METHYLCARBOMYL) OXIDE) & PLANTED IN THE GREENHOUSE ABSORBED 20% OF THE DOSE AFTER 1 DAY. THE SULFOXIDE AND SULFONE DERIVATIVES WERE THE PRIMARY PRODUCTS RECOVERED FROM PLANTS GROWN FROM THE TREATED SEEDS.
来源:Hazardous Substances Data Bank (HSDB)
代谢
三种代谢物:3,3-二甲基-1-(甲基硫酰基)-2-丁酮,O-((甲基氨基)甲酰基)氧基硫酰化物;3,3-二甲基-1-(甲硫基)-2-丁酮 O-((二甲氨基)甲酰基)氧基硫酸酯;以及3,3-二甲基-1-(甲硫基)-2-丁酮 O-((羟甲基氨基)甲酰基)氧基羟甲基硫酸酯,在大鼠中研究的这三种代谢物中,噻酚氧的羟甲基硫酸酯代谢物是最有效的,能够抑制血浆和红细胞乙酰胆碱酯酶。
OF THE THREE METABOLITES: 3,3-DIMETHYL-1-(METHYLSULFINYL)-2-BUTANONE, O-((METHYLAMINO) CARBONYL)OXIME SULFOXIDE; 3,3-DIMETHYL-1-(METHYLSULFONYL)-2-BUTANONE O-((DIMETHYLAMINO)CARBONYL)OXIME SULFONE; AND 3,3-DIMETHYL-1-(METHYLSULFONYL) -2-BUTANONE O-((HYDROXYMETHYLAMINO)CARBONYL)OXIME HYDROXYMETHYL SULFONE, INVESTIGATED IN RATS, THE HYDROXYMETHYL SULFONE METABOLITE OF THIOFANOX WAS THE MOST POTENT METABOLITE TO INHIBIT PLASMA & RED BLOOD CELL ACETYLCHOLINESTERASE.
来源:Hazardous Substances Data Bank (HSDB)
代谢
代谢的主要途径似乎是硫代氧化酶转化为其亚砜,随后进一步氧化为其砜。初始反应的速率明显快于第二个反应,特别是在植物中。还观察到氨基甲酰部分水解为相应的羟肟酸。基于LD50值,在大鼠中亚砜基氨基甲酸酯的毒性比硫代氧化酶及其相关化合物要大。
The major route of metabolism appears to be the oxidation of thiofanox to its sulfoxide & the subsequent oxidation to its sulfone. The rate of the initial reaction is decisively more rapid than that of the second, particularly in plants. Hydrolysis of carbamoyl moieties to their resulting oximes is also observed. ... Sulfonyl oxime carbamate is ... /more/ toxic /than thiofanox & related compounds in rats based on LD50 values/.
来源:Hazardous Substances Data Bank (HSDB)
代谢
氨基甲酸酯通过肝脏酶促水解;降解产物通过肾脏和肝脏排出。
The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
Thiofanox是一种胆碱酯酶或乙酰胆碱酯酶(AChE)抑制剂。氨基甲酸酯通过与酶的活性位点上的氨基甲酸化形成与胆碱酯酶的不稳定复合物。这种抑制作用是可逆的。胆碱酯酶抑制剂抑制乙酰胆碱酯酶的作用。由于其基本功能,干扰乙酰胆碱酯酶作用的化学物质是强效的神经毒素,即使在低剂量下也会导致过度流涎和眼泪。在更高剂量的暴露下,头痛、流涎、恶心、呕吐、腹痛和腹泻常常是显著的症状。乙酰胆碱酯酶分解在神经和肌肉接头释放的神经递质乙酰胆碱,以使肌肉或器官得以放松。乙酰胆碱酯酶抑制作用的结果是乙酰胆碱积聚并继续发挥作用,使得任何神经冲动持续传递,肌肉收缩不会停止。
Thiofanox is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌物分类
对人类不具有致癌性(未被国际癌症研究机构IARC列名)。
No indication of carcinogenicity to humans (not listed by IARC).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 健康影响
急性暴露于胆碱酯酶抑制剂可能会导致胆碱能危象,表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、崩溃和抽搐。肌肉无力可能性增加,如果呼吸肌肉受累,可能会导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处烟碱表达的过度刺激。当这种情况发生时,可以看到肌肉无力、疲劳、肌肉痉挛、肌肉颤动和麻痹的症状。当自主神经节积累乙酰胆碱时,这会导致交感系统中烟碱表达的过度刺激。与此相关的症状是高血压和低血糖。由于乙酰胆碱积累,中枢神经系统中烟碱乙酰胆碱受体的过度刺激会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力,甚至可能昏迷。当由于副交感神经乙酰胆碱受体处乙酰胆碱过多而出现毒蕈碱过度刺激时,可能会出现视力障碍、胸部紧绷、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。长期高(>10年)暴露会导致神经心理学后果,包括感知和视觉运动处理的干扰(A15321)。
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 暴露途径
吸入(L793);口服(L793);皮肤给药(L793)
Inhalation (L793) ; oral (L793); dermal (L793)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 症状
与有机磷化合物一样,症状和体征基于过度的胆碱能刺激。与有机磷中毒不同,氨基甲酸酯中毒的持续时间往往较短,因为神经组织乙酰胆碱酯酶的抑制作用是可逆的,且氨基甲酸酯的代谢速度更快。肌肉无力、眩晕、出汗和轻微的身体不适是常见的早期症状。头痛、流涎、恶心、呕吐、腹痛和腹泻在较高暴露水平时常常更为明显。瞳孔收缩伴视力模糊、不协调、肌肉抽搐和言语不清也有报道。(L795)
As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)
来源:Toxin and Toxin Target Database (T3DB)

文献信息

  • Electronic ID database and detection method for pesticide compound in edible agro-products based on LC-Q-Orbitrap
    申请人:CHINESE ACADEMY OF INSPECTION AND QUARANTINE
    公开号:US11169128B2
    公开(公告)日:2021-11-09
    Disclosed is an electronic ID database and detection method for pesticide compound in edible agro-products based on LC-Q-Orbitrap. The electronic ID database includes a collection of various pesticides compound electronic ID information, intelligent matching values and collision energies. It is ordered according to the retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, adduct ions information, fragment ions information, collision energies, and the optimal full scan mass spectrum. The detection method includes sample pre-treatment, setting LC-Q-Orbitrap operating conditions and sample pesticide residue screening. Setting LC-Q-Orbitrap operating conditions contain setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find pesticide compounds electronic ID database. If matching, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is same, the result is recorded and displayed, and the screening is completed.
    本发明公开了一种基于 LC-Q-Orbitrap 的食用农产品中农药化合物电子 ID 数据库及检测方法。电子 ID 数据库包括各种农药化合物电子 ID 信息、智能匹配值和碰撞能量的集合。它根据电子 ID 的保留时间进行排序。电子 ID 包含农药化合物信息、保留时间、加成离子信息、碎片离子信息、碰撞能量和最佳全扫描质谱。检测方法包括样品预处理、设置 LC-Q-Orbitrap 运行条件和样品农药残留筛选。设置 LC-Q-Orbitrap 运行条件包括设置合适的色谱和质谱条件。在农药残留筛选程序中,首先利用保留时间查找农药化合物电子 ID 数据库。如果匹配,则提取相应的电子 ID 信息。然后比较智能匹配值,如果相同,则记录并显示结果,完成筛选。
  • Electronic ID database and detection method for pesticide compounds in edible Agro-products based on GC-Q-Orbitrap
    申请人:CHINESE ACADEMY OF INSPECTION AND QUARANTINE
    公开号:US11181512B2
    公开(公告)日:2021-11-23
    Disclosed is an electronic ID database and detection method for pesticide compounds in edible agro-products based on GC-Q-Orbitrap. The electronic ID database includes a collection of various pesticide compounds electronic ID information and is sorted according to retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, mass spectrum, fragment ions information and intelligent matching value. The detection method includes sample pretreatment procedures, setting GC-Q-Orbitrap operating conditions and screening procedures for pesticide residues in samples, wherein setting GC-Q-Orbitrap operating conditions includes setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find out pesticide compounds in electronic ID database. If there is a match, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is less than threshold value, the result is recorded and displayed, and the screening is completed.
    本发明公开了一种基于 GC-Q-Orbitrap 的食用农产品中农药化合物电子 ID 数据库和检测方法。电子标识数据库包括各种农药化合物电子标识信息的集合,并根据电子标识中的保留时间进行排序。电子 ID 包含农药化合物信息、保留时间、质谱、碎片离子信息和智能匹配值。检测方法包括样品前处理程序、GC-Q-Orbitrap 操作条件设置和样品中农药残留筛选程序,其中 GC-Q-Orbitrap 操作条件设置包括设置合适的色谱和质谱条件。在农药残留筛选程序中,首先利用保留时间在电子 ID 数据库中查找农药化合物。如果匹配,则提取相应的电子 ID 信息。然后比较智能匹配值,如果小于阈值,则记录并显示结果,完成筛选。
  • Methods and compositions for increasing the efficacy of biologically-active ingredients
    申请人:Windsor Brian J.
    公开号:US20060276339A1
    公开(公告)日:2006-12-07
    The invention provides methods and compositions for modulating the sensitivity of cells to cytotoxic compounds and other active agents. In accordance with the invention, compositions are provided comprising combinations of ectophosphatase inhibitors and active agents. Active agents include antibiotics, fungicides, herbicides, insecticides, chemotherapeutic agents, and plant growth regulators. By increasing the efficacy of active agents, the invention allows use of compositions with lowered concentrations of active ingredients.
  • ELECTRONIC ID DATABASE AND DETECTION METHOD FOR PESTICIDE COMPOUNDS IN EDIBLE AGRO-PRODUCTS BASED ON GC-Q-ORBITRAP
    申请人:CHINESE ACADEMY OF INSPECTION AND QUARANTINE
    公开号:US20210285921A1
    公开(公告)日:2021-09-16
    Disclosed is an electronic ID database and detection method for pesticide compounds in edible agro-products based on GC-Q-Orbitrap. The electronic ID database includes a collection of various pesticide compounds electronic ID information and is sorted according to retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, mass spectrum, fragment ions information and intelligent matching value. The detection method includes sample pre-treatment procedures, setting GC-Q-Orbitrap operating conditions and screening procedures for pesticide residues in samples, wherein setting GC-Q-Orbitrap operating conditions includes setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find out pesticide compounds in electronic ID database. If there is a match, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is less than threshold value, the result is recorded and displayed, and the screening is completed.
  • ELECTRONIC ID DATABASE AND DETECTION METHOD FOR PESTICIDE COMPOUND IN EDIBLE AGRO-PRODUCTS BASED ON LC-Q-ORBITRAP
    申请人:CHINESE ACADEMY OF INSPECTION AND QUARANTINE
    公开号:US20210223219A1
    公开(公告)日:2021-07-22
    Disclosed is an electronic ID database and detection method for pesticide compound in edible agro-products based on LC-Q-Orbitrap. The electronic ID database includes a collection of various pesticides compound electronic ID information, intelligent matching values and collision energies. It is ordered according to the retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, adduct ions information, fragment ions information, collision energies, and the optimal full scan mass spectrum. The detection method includes sample pre-treatment, setting LC-Q-Orbitrap operating conditions and sample pesticide residue screening. Setting LC-Q-Orbitrap operating conditions contain setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find pesticide compounds electronic ID database. If matching, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is same, the result is recorded and displayed, and the screening is completed.
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